It’s an unseasonably balmy February day in Chicago, and Virgil Abloh is at the wheel of his black Bentley, giving me what I hope will be a tour of a few favorite hometown spots. The 19-year-old rapper XXXTentacion is blasting from the speakers.

“This new kid that everyone’s listening to. Have you heard of him?” he asks me generously, knowing the answer. “He blew up while he was in jail. I just love the climate where a record label could spend millions of dollars on trying to make someone the next big artist, and then this kid gets big with just having a badly produced song on the radio.”

Circumventing the gatekeepers is something Abloh has experienced firsthand: When, in 2009, he attended one of his first fashion shows, Comme des Garçons, as Kanye West’s creative director, he considered himself an outsider. “We got into about 60 percent of the shows,” he recalls of their arrival on the Paris scene. “We were a generation that was interested in fashion and weren’t supposed to be there. We saw this as our chance to participate and make current culture. In a lot of ways, it felt like we were bringing more excitement than the industry was.”

Fast forward to 2017. Abloh has been a key member of West’s brain trust for some 14 years—since interning with him at Fendi in 2009—but these days Abloh’s focus is Off-White c/o Virgil Abloh. With its bold high-low mash-up and signature diagonal black and white stripes, the label is worn by everyone from Kendall Jenner and Beyoncé to club kids from New York to Nigeria.

Abloh launched Off-White in 2013 and quickly drew notice; in 2015, he was the only American to become a finalist for the prestigious LVMH Prize for Young Fashion Designers. En route, he helped streetwear storm the luxury sector to take its place alongside it—without losing his cred. Off-White is sold at stores like Barneys New York and Colette, not to mention the Off-White boutique–cum–hangout spots that Abloh has designed in Tokyo, Hong Kong, and other cities. The first Off-White store in the U.S. opens in New York’s SoHo this summer.

Virgil Abloh (bottom right), at one of his favorite design galleries, the Carpenters Workshop Gallery, in Paris, surrounded by some of his friends and collaborators (clockwise, from top right): Acyde, Christina Paik, Tremaine Emory, Guillaume Berg, Adriana Mora, Luka Sabbat, and Arthur Karakoumouchian. Mora, Sabbat, and Paik wear clothes from the Off-White c/o Virgil Abloh fall 2017 collection; Abloh wears a hoodie from the same collection. The table is by the Dutch design duo Studio Job.

A canny translator of youth culture, Abloh is also an ever-present participant. Being “creatively schizophrenic,” as he describes himself, he has made incursions into so many realms that it’s hard to keep track: He deejays parties around the globe under the moniker Flat White, and, in 2016 alone, collaborated on collections with Moncler, Levi’s, VLONE, and the artist Brendan Fowler. He also presented his first line of furniture at Design Miami during Art Basel Miami Beach, and plans to publish books under his own imprint. Forthcoming are collaborations with Nike and an as-yet-unnamed major furniture retailer; there’s even a hotel in Asia in the works. In June, he will present his spring/summer 2018 men’s wear collection at Pitti Uomo, in Florence, following the likes of Raf Simons and Gosha Rubchinskiy, who have also shown there in recent years.

Abloh is unfailingly friendly and loves to chat—except that his casual conversation is peppered with references to the Bauhaus, Martin ­Margiela, and Ludwig Mies van der Rohe. On the breezy February day we first meet at the Mercer Hotel, in New York, rumors are swirling that he is a candidate to replace Riccardo Tisci in the top creative job at Givenchy; simultaneously, in an interview on GQStyle.com, Raf Simons has dismissed Abloh as unoriginal. Abloh has just returned from Berlin, where he was deejaying at Berghain, the club he calls the “most sacred of all electronic-music places.” But now he’s about to give a lecture on Abloh 101 titled “Everything in Quotes,” at Columbia University’s Graduate School of Architecture, Planning, and Preservation, where 200 people will be turned away and half the packed hall will be filled with cool kids dressed in vintage ’90s T-shirts and Supreme hoodies.

Abloh says that Simons has long been one of his heroes when I mention the GQStyle.com story. (Coincidentally, they are both nominated for a 2017 CFDA Award.) Still, he adds cautiously, “his critique shows the line in the sand” about youth culture—between the generation that dismisses hierarchies in fashion and the one that embraces streetwear as high fashion but doesn’t recognize streetwear’s pacesetters as peer designers.

A fashion shoot styled by Virgil Abloh in the Barcelona Pavilion designed by Mies van der Rohe. Photographed by Fabien Montique for a forthcoming book by Abloh of short stories through images.

Abloh, 36, straddles both points of view. He holds degrees in engineering and architecture but not fashion, and sees himself as part of the generation forging alternate routes to the top. “I don’t come from where I’m supposed to come from,” he says, explaining what fuels his drive. “So I have to prove that this is design, that this is art, that this is valid.”

His target audience is the post-Tumblr generation of kids raised on YouTube and social media who can name-check esoteric fashion brands and want to wear Off-White—or start their own labels. “I’m always ­trying to prove to my 17-year-old self that I can do creative things I thought weren’t possible,” he says, pausing to inspect the prototype he designed for a Nike Air Force 1 sneaker that’s just arrived in a box. The shoe, which he’ll later pass around to the Columbia students, features a swoosh collaged over Off-White’s telltale stark typeface. “Everything I do references something that influenced me.”

A series of books he’s working on ­features models wearing his clothes inside iconic architectural landmarks, such as Mies van der Rohe’s Barcelona Pavilion. “The idea is to teach my demographic about architecture through buildings that have inspired my way of thinking. I want to put culture on a track so that it becomes more inclusive, more open source. And then give kids the chance to ride in the express lane.”

He points to those in his inner circle who are impacting the music, art, and fashion worlds without being trained designers, all of them social media superinfluencers. They include the rapper A$AP Rocky, the ­creative director A$AP Bari, the underground artist Jim Joe, the teen model Luka Sabbat, and the stylist Ian Connor, the self-described King of the Youth. “Those kids don’t realize the power they have,” notes Abloh of ­Connor, 24, who has 769,000 Instagram followers, and Sabbat, 19, who has 397,000. (Abloh has 714,000.) “They could become more relevant than fashion brands. I say to them, ‘Kylie’s outfit is different because you exist.’ ”

Bella Hadid walks the runway during the Off-White show during Paris Fashion Week F/W '17.

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His style of creative direction “is to find and foster those relationships and plug them into the system,” he says of the close-knit squad of disruptors he champions. He helped 34-year-old Heron Preston debut his first collection by setting him up with New Guards Group, the Milan-based company that produces Off-White. And in January, at his own men’s wear show, Abloh launched Off-White c/o Art Dad LLC, the capsule collection he created with Tremaine Emory and the DJ Acyde of the fashion-and-music collective No Vacancy Inn. Connor, the fashion-forward A$AP Mob collaborator, who has styled Wiz Khalifa and consulted for West, credits Abloh with teaching him to “think as a creative” and put his ideas into play. The two are at work on a book of Connor’s behind-the-scenes Polaroids that Abloh will publish this summer.

Philanthropy is another of his objectives. With Laurene Powell Jobs, the widow of Apple cofounder Steve Jobs, he’s planning to partner on an anti-violence initiative in Chicago aimed at mentoring unemployed youth in streetwear design.

Abloh launched his first label, Pyrex Vision, in 2012. On dead-stock Rugby Ralph Lauren flannel shirts that he bought at a discount, he screen-printed the word pyrex and sold them for $550 apiece. (Connor co-styled the look book, and Jim Joe directed a film.) Since 2014, the designer has shown his Off-White collections only in Paris— he dubs it fashion’s “home court” —and upped his game with sharp tailoring, velvet down jackets, and shearling coats made in Italy. “My idea was that something niche would be elevated to the point where it’s worthy of putting on a Paris runway,” he says. A case in point is the organza hoodie he shows me on his iPhone when we meet the following week in Chicago. In response to Simons’s comments, he says, he redesigned his entire fall women’s collection “to turn the dial up”; now it is titled “Nothing New,” a nod to the reappropriation that runs through fashion. The Women’s March in Washington, D.C., inspired him to make cropped jackets meant to suggest protective armor, as well as luxuriantly flowing dresses of organza and georgette, with embedded plastic panels, as a way to insert the idea of street “in a more abstract way.”

He makes no secret of his desire to run a storied luxury house, though by then Givenchy has publicly denied approaching Abloh. (The job eventually went to Claire Waight Keller.) In Demna Gvasalia, 36, the Georgian designer behind Vetements and Balenciaga, Abloh finds a kindred spirit, recalling that the two hung out in January following the Balenciaga afterparty, at which Abloh DJ'ed.

“Neither of us subscribes to a certain fauxness that is status quo in the fashion world,” says Abloh, who is wearing a black Balenciaga denim jacket, an O32c T-shirt, Supreme pants, and Adidas NMD sneakers.

Abloh’s first muse is his wife, Shannon, whom he met in high school and married in 2009. The couple live in Chicago’s Lincoln Park with their daughter, Lowe, 4, and son, Grey, 1, but Abloh admits he’s rarely in town for very long. He flies more than 350,000 miles a year—and in economy when he’s paying. The previous afternoon he had been at West’s relatively low-key Yeezy Season 5 show, in New York; afterward he’d returned home for his daughter’s school recital.

“Those things I don’t miss,” he says. “My sacrifice is: I’m down to fly.” In a day he’ll be off to DJ a party in D.C., then another in Las Vegas, before ­heading to Milan and Paris, with his travelogue and mood boards strategically rolled out on social media. For the moment he decides to head to Volume Gallery, a contemporary-design space run by a friend of his. His home is still a work in progress, furnished with a mix of pieces by Pierre Jeanneret and Rick Owens, he tells me, but when I suggest we stop by, he hesitates.

“I don’t want to be a celebrity designer. I want to keep my personal life out of it.”

As the son of Ghanaian immigrants growing up in the middle-class Chicago suburb of Rockford, Abloh had assumed that he’d end up in an office job. His dad managed a paint company, his mother was a seamstress. Abloh was into skateboarding, Air Jordans, and hip-hop, though he keenly recalls his mother cutting out paper patterns and making ­garments from scratch for the stream of customers who marched through their home. At his predominantly white Catholic high school, he played varsity soccer and wore a uniform. The button-down shirt and blazer with gold buttons “gave me Fresh Prince of Bel-Air vibes,” he says. His parents let him DJ on the weekends, though they expected him to settle on a respectable profession, which is how he landed at the University of Wisconsin studying civil engineering. In his free time, he read fashion magazines and DJ'ed.

In his final semester, he took his first art-history class, and the discovery of the Renaissance, Caravaggio—and the notion that innovation was possible within a creative discipline—“blew my mind.” So did his immersion in the work of Mies van der Rohe and Rem Koolhaas at the Illinois Institute of Technology, where he earned his graduate degree in architecture. On the side, he made graphic T-shirts, started his own website, and engineered a crucial meeting with West by finding out where the rapper screen-printed his merchandise. Incorporating West’s G.O.O.D. Music logo on a line he designed for him voluntarily, Abloh left a printout of looks at the shop, where they caught the eye of the owner, whom Abloh later persuaded to call West’s then-manager.

A month later, Abloh was traveling the globe with West. “We’re all the children of Kanye’s trailblazing,” Abloh says. “This generation wouldn’t have the freedom to cross genres had it not been for his passion to find more than what was delivered to him.”

Of course, Abloh helped West forge that path, by concretizing some of West’s hugely ambitious ideas. The graphic designer Michael Rock recalls Abloh’s agility at mobilizing the many strong and disparate personalities involved. “He was the glue,” says Rock, whose design firm 2x4 worked with Koolhaas’s OMA to build the concept and seven-screen pavilion for West’s 2012 debut short film, Cruel Summer, which premiered at the Cannes Film Festival.

“Virgil can slip into a celebrity entourage and also have a really serious conversation with an architect. Not many people can bridge those worlds.”

The art museum is his next frontier. In 2019, the Museum of Contemporary Art Chicago will present Abloh’s first retrospective. A major homecoming of sorts, the show will highlight “the Möbius strip of activity that has made Virgil a kind of Renaissance man,” says its curator, Michael Darling.

When Abloh got the message that Darling had contacted him last summer, he assumed the museum wanted him to DJ a party. “So I’ve spent this time proving to myself that I’m worthy to show as an artist,” he says. DJ'ing, in any case, is an apt metaphor for what Abloh does best: “It’s on the fly,” he says.

“You have three minutes to read the room, play a song, and impress the crowd. Then you have to figure out how to style this group of songs together so it’s one point of view. I’m literally just litmus-testing the culture.”